Ethyl piperidine-2-carboxylate → 1-(2-Fluoro-4-chloro-5-isopropoxycarbonylphenyl)aminocarbonyl-2-ethoxycarbonylpiperidine

HRID 371361Notes

Reaction equation

HRID 371361 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[CH:6][C:5]([N:14]=[C:15]=[O:16])=[C:4]([F:17])[CH:3]=1.[NH:18]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[CH:6][C:5]([NH:14][C:15]([N:18]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:16])=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 27517Ethyl piperidine-2-carboxylateHCID 13519895Isopropyl 2-chloro-4-fluoro-5-isocyanatobenzoate

Product 1

HCID 155899051-(2-Fluoro-4-chloro-5-isopropoxycarbonylphenyl)aminocarbonyl-2-ethoxycarbonylpiperidineYield 83.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.15 g (0.02 mol) of 4-chloro-2-fluoro-5-isopropoxycarbonylphenyl isocyanate were added to a solution of 3.31 g (0.02 mol) of ethyl pipecolate (95% purity) dissolved in 30 ml of benzene. The mixture was stirred at room temperature for an hour, washed with water, dried over anhydrous sodium sulfate, and then concentrated. The resulting crystal was recrystallized from a mixed solvent of hexane, toluene and ethyl acetate to give 6.9 g (yield 83.2%) of the desired product as white crystals with a melting point of 83°-85° C.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting crystal was recrystallized from a mixed solvent of hexane, toluene and ethyl acetate

Sources & evidence

ORD record
ord-5b5d0d5ac3fe4032befd8d21546ad2f3
Source dataset
uspto-grants-1985_07
Patent number
US04531964

Reaction notes

Loading…